3-chlorobenzenecarbothioamide

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 340 mg of 3-chlorothiobenzamide was dissolved in 10 ml of ethanol, 570 mg of diethyl bromomalonate was added to the solution, and the mixture was heated at 60° C. for 2 hours. After the reaction mixture was cooled, and the resulting crystal was collected by filtration and recrystallized from ethanol to give 408 mg of ethyl 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylate. This product was hydrolyzed by a conventional process to give 306 mg of 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylic acid (yield: 60%). After the reaction mixture was cooled the resulting crystal was collected by filtration recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is prepared analogously to the process described in Example 1c using 2-bromo-5-chloroindan-1-one and 3-chlorothiobenzamide; melting point: 205-210° C. (dec.). This compound is prepared analogously to the process

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is prepared analogously to the process described in Example 1c using 2-bromo-5-chloroindan-1-one and 3-chlorothiobenzamide; melting point: 205-210° C. (dec.). This compound is prepared analogously to the process

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the alpha-bromoketone from step 4 (1.0 eq) in DMF (0.1M) was added 3-chlorobenzenecarbothioamide (1.0 eq). The mixture was heated at 40-120° C. for 1-3 h, cooled, diluted with water, saturated NaHCO3 solution and ether. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (Hexane:EtOAc) to afforded the title compound. cooled The organic extracts were washed with brine dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (Hexane:EtOAc)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 340 mg of 3-chlorothiobenzamide was dissolved in 10 ml of ethanol, 570 mg of diethyl bromomalonate was added to the solution, and the mixture was heated at 60° C. for 2 hours. After the reaction mixture was cooled, and the resulting crystal was collected by filtration and recrystallized from ethanol to give 408 mg of ethyl 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylate. This product was hydrolyzed by a conventional process to give 306 mg of 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylic acid (yield: 60%). After the reaction mixture was cooled the resulting crystal was collected by filtration recrystallized from ethanol